Days removed from a second-straight win to close out April, Toronto FC were back at it, welcoming the most testing month of the season as May brought with it six league matches as well as the opening series in the 2017 Canadian Championships for a total of eight fixtures in some 28 days.
Before the action kicked off, another signing was completed as striker Ben Spencer joined the first team on May 2.
The next day, TFC welcomed Orlando City SC to BMO Field, extending their winning streak with a 2-1 result on May 3.
Sebastian Giovinco was at it again, scoring a pair of first half goals before Orlando's Kaka pulled one back before the half-time whistle. Two jaw-dropping saves from Alex Bono prevented Cyle Larin from equalizing in the second half to ensure that Greg Vanney's 100th match at the helm of the club was a victorious one.
With three of the next four matches on the road, there was little time to savour the milestone, as the side braced for an MLS Cup rematch against Seattle Sounders FC on May 6.
In a glimpse of things to come, Vanney went with a previously unseen formation, as TFC got a modicum of revenge against Sounders FC, winning 1-0 courtesy of a Jozy Altidore penalty kick, powering his effort past Stefan Frei.
That would not be the day that observers would see a match between these two decided by a goal from open-play, though such a day would come.
Frei did get in a subtle reminder of the previous December with a stunning save on an Altidore blast, but Toronto would savour the three points nonetheless.
The winning streak reached five, setting a new club record, come May 10 with another visit to Columbus, beating Crew SC 2-1 thanks to a pair of influential substitutes, as Tosaint Ricketts scored twice in the final ten minutes, each set up by Raheem Edwards, to overturn a cheeky first-half penalty kick from Federico Higuain.
A fifth match in quick succession fell on May 13 back at BMO Field, where expansion side Minnesota United proved a stern test, only for Ricketts to again nab a late game-winner in a 3-2 victory, Altidore and depth again credited with extending the club record streak to six wins, prompting a special episode of All for One, rife with foreshadow.
But six is all it would reach, as on May 19 the club would settle for a 1-1 draw away to the New York Red Bulls, as Bradley Wright-Phillips and Benoit Cheyrou exchanged blows. Toronto had a chance to extend the run to seven, but Luis Robles was able to parry Altidore's late penalty kick and Ricketts' magic ran out, as he could only rattle the bar as the clock ticked down.
On a more positive note, that same match saw Drew Moor return from the scare forced him to the sideline for a little over a month.
Up next was the first-ever Battle of Ontario as TFC faced off against Ottawa Fury FC in the semifinals of the Voyageurs Cup on May 23 in the nation's capital.
Fury FC got the better of a sloppy TFC on the day, with TFC II's Mitch Taintor unlucky on both Ottawa goals, the first a penalty and the second a deflection to overturn a well-worked Cheyrou strike in the first half.
Toronto would salve those wounds on May 26 with a 5-0 dismantling of Columbus in the deciding match of the Trillium Cup. Victor Vazquez was the star on the night, opening the scoring from the penalty spot before sneaking a free-kick under the leaping Crew SC wall, prompting Vanney to herald the Catalan as 'the most clever mid' in MLS. In his debut, Spencer showed some excellent hustle to force a turnover and find Justin Morrow in space for the second of the night. Jonathan Osorio and Jordan Hamilton added further blushes late.
And finally, on the last day of the month, Toronto would close it out in style, overturning Ottawa's first-leg advantage with a 4-0 win on May 31 to ensure they would meet Montreal in the Voyageurs Cup Final.
It was not a night without concern, as Ottawa held firm for 40 minutes before a dangerous Tsubasa Endoh ball into the area forced an own-goal out of Fury defender Eddie Edward. Endoh then added a second in short-order; depth once more the star.
Still, the series was finely-balanced until Marky Delgado put it out of reach late and Giovinco added the coup de grace in the final minutes.